Dave Chappelle Is the Comedic Voice Trump's America Deserves

In 2006, during an interview with Oprah Winfrey, Dave Chappelle told his onetime sketch-comedy target: "I was doing sketches that were funny but socially irresponsible. I felt like I was deliberately being encouraged, and I was overwhelmed. It's like you're being flooded with things and you don't pay attention to things like your ethics."

Chappelle's work has always been guided by his comic instincts and a love of marijuana so pervasive that he wrote an entire film about it, 1998’s Half-Baked. But he’s also been led by a comedic moral compass. With an eye for spotting social injustice, Chappelle is incredibly adept at observational humor that levies its assaults upon bigotry, inequality, and all forms of racism. He confronts these subjects in hilarious and often uncomfortable (for audiences) ways.

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That's just the kind of comedy America needs these days. Ahead of Chappelle's gig at the Coral Springs Center for the Arts this Friday, New Times looks back at his most insightful and incisive commentary, now just as relevant as ever.

“Monologue”

There could not have been a better time or place for Chappelle to return to his sketch-comedy days than the first Saturday Night Live episode after the election of Donald Trump. Combining a fearless, outspoken, topical comic such as Chappelle with a cast and writing staff that have proven to be equally ballsy the past several seasons was a coup for producer Lorne Michaels and company.

During his nearly 12-minute opening monologue, Chappelle takes the obvious jabs at the election, Trump, and the outrage by half of America. However, between jokes, Chappelle also reminds us that we cannot forget about mass shootings and the epidemic of police shootings of black Americans (of course he can’t help inserting a joke even here, saying, “Now I admit, ‘Black lives matter’ is not the best slogan, but McDonald’s already took ‘You deserve a break today.’”) He ends the monologue with a hopeful, if cautious, sentiment after waxing nostalgic about a White House party attended entirely by black people (plus Bradley Cooper, for some reason). He says, “In that spirit, I’m wishing Donald Trump good luck, and I’m going to give him a chance. And we, the historically disenfranchised, demand that he give us one too.” It’s a powerful statement that searches for a glimmer of unity and offers support contingent upon it going both ways.

“Election Watch Party”

In that same SNL episode, Chappelle skewered white liberal America's reaction to Trump's win in "Election Watch Party." There’s a point in this sketch featuring Chappelle and several upper-middle-class white characters where someone comments, “Well, of course, he won Kentucky; I mean that’s where all the racists are,” to which Chappelle’s character responds with a dubious “All of them are in Kentucky?” It encapsulates the miscalculation by liberal pundits, media pollsters, and the Clinton campaign (all mostly white) in assuming they understood the true nature of so many Americans. The outcome at the close of the bit, Trump’s election, might come as a shock to the white partygoers, but not to Chappelle or surprise guest Chris Rock, who like the rest of black America knows all too well the racism that still afflicts our country.

Chappelle’s Show

Aside from being perhaps one of the most quotable TV programs of the past half-century, Chappelle’s Show brazenly and unflinchingly explored race in a way that had been done only with politically incorrect jokes told confidentially among friends. The show used the word “nigger” with a frequency and ownership that felt like a feat, not a slur.

It's impossible to choose just one sketch to represent the entirety of Chappelle's Show. Sketches such as “Celebrity Trial Jury Selection,” “Race Draft,” “The Niggar Family,” and “Reparations” assaulted prejudice and stereotypes in a way that exposed people on all sides of ethnicity – black, white, Asian, Hispanic, etc. – as guilty of one thing or another.

Arguably, the most famous sketches from Chappelle’s Show are the one featuring Charlie Murphy and his stories about Prince and Rick James. It spawned catchphrases like “Game. Blouses” and “I’m Rick James, bitch!” Still, Chappelle’s most iconic, and perhaps most important, sketch might just be the one that began the entire series: “Frontline: Clayton Bigsby.”

The story of the blind white supremacist who just happened to be black was controversial, outrageous, and set the tone for the next two seasons. It also happens to be the most telling. After Bigsby finds out he’s actually African-American (and that one Ku Klux Klan member’s head explodes), he removes himself from the movement. He does one other thing that brings home the point of the sketch: He divorces his wife after 19 years of marriage. When the newsman asks him why, Bigsby answers simply, “Because she’s a nigger lover.” There might be no starker, truer, or funnier commentary on the deep-seeded nature of racism in the United States.

In many ways, Killin’ Them Softly is Chappelle’s manifesto. His masterpiece is Chappelle’s Show, but this standup special from 2000 is the creative genesis from which the rest emerged. Much of the special is centered on race and race relations between whites and blacks, cops and blacks, and members of the black community themselves.

He also takes time to address the public’s attitude and general dismissal of homeless people: “But now I'm watching it as an adult, and I realize that Sesame Street teaches kids other things. It teaches kids how to judge people and label people. That's right. They got this one character named Oscar. They treat this guy like shit the entire show. They judge him right to his face. ‘Oscar, you are so mean. Isn't he, kids?’ ‘Yeah. Oscar, you're a grouch!’ He's, like, ‘Bitch, I live in a fucking trash can! I'm the poorest motherfucker on Sesame Street. Nobody is helping me.’ Now you wonder why your kids grow up and step over homeless people, like, ‘Get it together, grouch. Get a job, grouch.’”

He also comments on the disparate way in which Cubans (an island with a population that is about two-thirds white) and Haitians (mostly black) are treated. “All I gotta say about Elián is, thank God he's Cuban. 'Cause if he had been Haitian, you'd have never heard about his ass. If Elián González was Elián Mumoombo from Haiti, they'd have pushed that little rubber tube back into the water. ‘Sorry, fella. All full.’”

Perhaps his greatest contribution from Killin’ Them Softly, one that's eerily prescient in 2017, is his commentary on police violence toward African-Americans. According to an article in the NY Daily News, “Trump’s first month in office ended with at least 105 people killed by American police. That’s the highest number of people killed by American police in any one month since 2015.”

Like Richard Pryor before him, Chappelle urges safety when black people speak to the police. In fact, he has a very elementary piece of advice: “Every group of brothers should have at least one white guy – I'm serious – for safety. 'Cause when the shit goes down, somebody's gonna need to talk to the police.”

He goes on to recount his own adventures with his white friend Chip and their interactions with the police. Chappelle describes instances of being high while asking cops for directions and later racing a police cruiser, yet Chip faces no consequences. It’s an exaggeration, of course, but these absurd examples make an important point about law enforcement's uneven treatment of blacks and whites.

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Even when Chappelle understands the need to call the police when he has been the victim of a crime, his cultural instincts kick in. He imagines a scenario where cops come to his home after a burglary: “Somebody broke into my house once; this is a good time to call the police, but, mm-mm, nope. The house was too nice. It was a real nice house, but they'd never believe I lived in it. They'd be like, 'He's still here!’"

Chappelle whacks the microphone on the stand, imitating an officer using his baton on Chappelle, the homeowner. "‘Oh my God. Open-and-shut case, Johnson. I saw this once when I was a rookie. Apparently, this nigger broke in and put up pictures of his family everywhere.'”

Chappelle's comedy garners laughs because it hews to the old adage “It’s funny because it’s true.” The terrible part of that last joke is many of us can imagine that scenario actually happening. And with life's daily distractions – work, family, school, bills, and Trump's incessant lies and accompanying tweets – it’s easy to forget some of the other things that are so important. Thank the comedy gods we have Dave Chappelle to remind us of the horror and make us laugh through the fear.

Angel Melendez is an unabashed geek and a massive music nerd who happens to write words (and occasionally take photos) for Miami New Times. A graduate of Florida Atlantic University and an accomplished failure at two other universities, Angel is a lush and an insufferable know-it-all, and has way better taste in music than you. His wealth of useless knowledge concerning bands, film, and Batman is matched only by his embarrassingly large collection of Hawaiian shirts and onesies.